Lanostane triterpenoids from fruiting bodies of basidiomycete Stereum sp., structures and biological activities

Abstract

Twelve new lanostane triterpenoids, sterenoids A-L (1-12) have been isolated from fruiting bodies of the basidiomycete Stereum sp. Compounds 1-12 are rare 14(13→︀12)abeo-lanostane triterpenoids featuring remarkable 13R configurations that discriminate from the previously covered counterparts. Their structures and absolute configurations are assigned on the basis of in-depth one- and two-dimensional NMR spectroscopic analysis, as well as unbiased quantum chemical NMR and electronic CD calculations. All isolates are evaluated for their in vitro cytotoxicity against five human tumor cell lines. Compound 5 exhibits potent cytotoxic activities against tumor cell lines HL-60 and SMMC-7721 with IC values of 4.7 and 7.6 μM, respectively.

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

“…Sterenoids A–L (182–193), twelve lanostane triterpenoids, have been obtained from fruit bodies of Stereum sp. [ 98 ], and their absolute configurations were confirmed by unbiased quantum chemical NMR and ECD calculations. The 13R configuration in these compounds features a distinctive and rare 14(13→12) abeo -lanostane type [ 99 , 100 ].…”

“…The 13R configuration in these compounds features a distinctive and rare 14(13→12) abeo -lanostane type [ 99 , 100 ]. Sterenoid E (186) exhibited effective cytotoxicity against tumor cell lines SMMC-7721 and HL-60 with IC 50 values of 7.6 and 4.7 μM, respectively [ 98 ]. Stereinones A–J (194–203), ten highly-oxygenated lanostane triterpenoids, were obtained from the Stereum sp.…”

Bioactive Usual and Unusual Triterpenoids Derived from Natural Sources Used in Traditional Medicine

“…Ubiquitous fungus, acclaimed as high‐performance natural occurrence builders, produce an abundance of secondary metabolites with various novel scaffolds and biological processes [29] . From the basidiomycete Stereum sp., buds isolated and identified several sterenoids A–L are lanostane triterpenoids.…”

“…From the basidiomycete Stereum sp., buds isolated and identified several sterenoids A–L are lanostane triterpenoids. Among these, sterenoid E ( 66 ) has substantial cytotoxic effects on the tumor cell lines, including SMMC‐7721 and HL‐60 cell lines, with IC 50 values of 7.6 and 4.7 μM, respectively [29] …”

“…Hopanes are unstable and widely found in biological sludge, and 21αH hopanes or moretanes resulted from cyclization of squalene in 1-boat and 4chair conformation. The backbone rearmament of moretane affords neomotiane or neohopane (27), fernane (28), adianane (29), and filicane (30) skeletons. [5] Stictane (31) is made by cyclizing squalene or its 2,3-epoxide in the chair-boar-chair-chair-boat conformation and then expanding the E ring, and backbone rearrangement yielded arborinane (32) skeletons.…”